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Chemistry
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4-Chlorothieno[3,2-d]pyrimidine-7-carboxylic acid
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[ CAS No. 1269667-57-3 ] {[proInfo.proName]}

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Chemical Structure| 1269667-57-3
Chemical Structure| 1269667-57-3
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CAS No. :1269667-57-3 MDL No. :MFCD20926153
Formula : C7H3ClN2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 214.63 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1269667-57-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1269667-57-3 ]

[ 1269667-57-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 31169-25-2 ]
  • [ 1269667-57-3 ]
Reference： [1]Patent: WO2011/25940,2011,A1
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 2869 - 2881
  • 2
  • [ 175137-13-0 ]
  • [ 1269667-57-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 1 h / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; dimethyl sulfoxide / 0 - 20 °C
Multi-step reaction with 6 steps 1: trichlorophosphate / 2 h / 110 °C 2: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 100 °C 3: potassium iodide / N,N-dimethyl-formamide / 4 h / 35 °C 4: water; sodium hydroxide / tetrahydrofuran / 0.5 h 5: manganese(IV) oxide / chloroform / 2 h / 70 °C 6: sodium dihydrogenphosphate dihydrate; sodium chlorite / water; dimethyl sulfoxide / 0 - 20 °C
Reference： [1]Current Patent Assignee: HANMI PHARM CO LTD; HANMI SCIENCE CO LTD - WO2011/93672, 2011, A2 Current Patent Assignee: HANMI SCIENCE CO LTD; CATHOLIC UNIVERSITY OF KOREA; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - WO2011/93684, 2011, A2 Current Patent Assignee: HANMI PHARM CO LTD; HANMI SCIENCE CO LTD - US2012/302567, 2012, A1
[2]Current Patent Assignee: HANMI SCIENCE CO LTD; CATHOLIC UNIVERSITY OF KOREA; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - US2013/53370, 2013, A1
  • 3
  • [ 651734-54-2 ]
  • [ 1269667-57-3 ]
  • [ 1318133-05-9 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20℃; for 15h; 4-Chlorothieno[3,2-d]pyrimidine-7-carboxylic acid(23mg, O.lOmmol) prepaed in step g of Example 107, <strong>[651734-54-2]2,6-difluoro-3,5-dimethoxybenzene amine</strong>(19mg, O.lOmmol), and HOBT (N-hydroxybenzotriazole, 13.5mg, O.lOmmol) were dissolved in acetonitrile(2mL), and EDCI (57mg, 0.30mmol) was added thereto at room temperature. - After 15 hrs, water and ethyl acetate were added to the reaction mixture. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saline solution, dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting concentrate was purified by silica gel chromatography (DCM:MeOH = 20: 1) to obtain the title compound. NMR (400MHz, DMSO-d6) delta 10.69(s, 1H), 9.39(s, 1H), 8.88(s, 1H), 7.02(s, 1H), 3.84(s, 6H).
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20℃; for 15h; a. 4-Chloro-N-(2,6-difluoro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide 4-Chlorothieno[3,2-d]pyrimidine-7-carboxylic acid (23 mg, 0.10 mmol) prepared in step g of Example 107, <strong>[651734-54-2]2,6-difluoro-3,5-dimethoxybenzene amine</strong> (19 mg, 0.10 mmol), and HOBT (N-hydroxybenzotriazole, 13.5 mg, 0.10 mmol) were dissolved in acetonitrile (2 mL), and EDCI (57 mg, 0.30 mmol) was added thereto at room temperature. After 15 hrs, water and ethyl acetate were added to the reaction mixture. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saline solution, dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting concentrate was purified by silica gel chromatography (DCM:MeOH=20:1) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) delta 10.69 (s, 1H), 9.39 (s, 1H), 8.88 (s, 1H), 7.02 (s, 1H), 3.84 (s, 6H).
Reference： [1]Patent: WO2011/93672,2011,A2 .Location in patent: Page/Page column 49; 50
[2]Patent: US2012/302567,2012,A1 .Location in patent: Page/Page column 22
  • 4
  • [ 175137-21-0 ]
  • [ 1269667-57-3 ]
Reference： [1]Patent: WO2011/93672,2011,A2
[2]Patent: US2013/53370,2013,A1

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